Retired Major General William Anders, the former Apollo 8 astronaut who took the iconic “Earthrise” photo showing the planet as a shadowed blue marble from space in 1968, was killed Friday when the plane he was piloting alone plummeted into the waters off the San Juan Islands in Washington state. He was 90. His son, Greg Anders, confirmed the death to The Associated Press.

“The family is devastated,” Greg Anders said. “He was a great pilot, and we will miss him terribly.”

Anders said the photo was his most significant contribution to the space program, given the ecological and philosophical impact it had, along with making sure the Apollo 8 command module and service module worked.

A report came in around 11:40 a.m. local time that an older-model plane had crashed into the water and had sunk near the north end of Jones Island, San Juan County Sheriff Eric Peter said.

Only the pilot was on board the Beech A45 airplane at the time, according to the Federal Aviation Association.

William Anders said in a 1997 NASA oral history interview that he didn’t think the Apollo 8 mission was risk-free but there were important national, patriotic and exploration reasons for going ahead.

He estimated there was about a one-in-three chance that the crew wouldn’t make it back and the same chance the mission would be a success and the same chance that the mission wouldn’t start to begin with. He said he suspected Christopher Columbus sailed with worse odds.

He recounted how the Earth looked fragile and seemingly physically insignificant yet was home.

“We’d been going backwards and upside down, didn’t really see the Earth or the sun, and when we rolled around and came around and saw the first Earthrise,” he said. “That certainly was, by far, the most impressive thing. To see this very delicate, colorful orb which to me looked like a Christmas tree ornament coming up over this very stark, ugly lunar landscape really contrasted.”

The National Transportation Safety Board and FAA are investigating the crash.